I want to make sure I have everything covered when I choose to do this.Thanks in advance for you advice!

In my head, someone else would be paying the majority of my mortgage while I'm paying super cheap rent and could cover rent/mortgage in case of an emergency. 

I would like to think they'd cover the damages though they may make you try to claim it through your insurance-which I wouldn't do as it was partly their fault. 

Try checking what the tax assessor thinks it's worth, and also what zillow thinks it's worth. 3) Will the cash flow from the 2 apartments cover the cost of the loan, taxes, insurance, repairs, and some on top for you?

That primarily covers it. 

Being that this is my first deal and I do not have a lot of cash having a property where several units are rented and I can rehab the property while the rents are covering the expenses.

And, after renting both units, the mortgage and expenses would be covered with  some cushion on top.

You would want to try and bring in $1000 per month to cover the mortgage in case the unit is vacant for a month or 2 while search for a replacement tenant.10.Hire property manager?

You would want to try and bring in $1000 per month to cover the mortgage in case the unit is vacant for a month or 2 while search for a replacement tenant.10.Hire property manager?

Not only will they not cover the damage to the room but it will void the insurance on your entire property.